olo: 30 days in



~3 min read


581 words

I recently crossed thirty days at Olo. I thought it would be valuable to pause for a few minutes to reflect my time so far, short as it is, as well as to think about what the future may hold.

The first thing that comes to mind is just how short thirty days is. At the same time, I feel like I’ve been here for a lot longer because of the interview cycle and the amazing pre-start communication I received.1

Before my first day, Olo had so many nice touches that really made me feel welcome. Emails from HR with a walk through of what to expect, individual notes from my future teammates welcoming me, and a swag package were just some of the highlights.

I’ve noticed that the weeks have naturally fallen into a very nice cadence. At the week level, we are actually practicing two-week sprints.2 We begin with sprint planning. We end with retrospectives and demos. Along the way we have stand ups and are constantly communicating. Tuesdays and Thursdays are quiet days though - which is great for focused work. Mondays, Wednesdays and Fridays have more meetings, which can fill up the day quickly. Even here though, it seems the culture is one of self-awareness and curiosity. We talk openly and frequently about the meetings that are scheduled and who’s in them to determine if they’re valuable uses of time.

The first thirty days have been a whirlwind. I’ve felt it, but, fortunately, everyone knows it. It’s expected. We call it a firehose and the analogy feels apt. Olo’s not brand new. We’ve been around longer than Twitter. Among other things, that means there’s a lot to learn. Olo’s business is also done behind the scenes to make things work and other folks look good. It’s not about showmanship or ego - it’s about results - and always striving for better.

The same spirit that goes into our products is also how we treat one another. My first month has been full of learning and pairing sessions. Pairing isn’t just a new hire thing either! Engineers on other teams have leaned in to help me and answer questions. A buddy program gives me a direct line to ask questions - related to my job and about the company generally - while introducing me to folks I wouldn’t otherwise interact with regularly.

After only thirty days, I’m still very new. I can feel that I’m very new. Many of my colleagues have years of experience with Olo (which is also one of the things I found most attractive when applying: people stick around). But I’m also starting to feel like I’m contributing real value. I can’t predict the future with any certainty (2020 seems to have ensured that I’ll never feel confident in making a forecast), but these first thirty days feel like a homecoming. It feels like after multiple stops and careers, I’ve found a place that really fits.


  • 1 I could wax poetic about the interview process at Olo. It took longer than I would have liked (global pandemics have a way of sowing uncertainty and upending expectations), but every step of the way felt great.
  • 2 I’m emphasizing actually because I’ve read a lot about agile workflows, I worked to implement them myself, I’ve worked at other places that say they work in an agile way, but I’ve not been on a team that seems to flow this well.

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  • Hi there and thanks for reading! My name's Stephen. I live in Chicago with my wife, Kate, and dog, Finn. Want more? See about and get in touch!